COPPER-INDUCED SYNTHESIS OF IMINIUMS - TRIMETHYLAMINE OXIDATION OR AMINE N-OXIDE CONVERSION

Authors
ROUSSELET G CAPDEVIELLE P MAUMY M
Citation
G. Rousselet et al., COPPER-INDUCED SYNTHESIS OF IMINIUMS - TRIMETHYLAMINE OXIDATION OR AMINE N-OXIDE CONVERSION, Tetrahedron letters, 36(28), 1995, pp. 4999-5002
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
28
Year of publication
1995
Pages
4999 - 5002
Database
ISI
SICI code
0040-4039(1995)36:28<4999:CSOI-T>2.0.ZU;2-Q
Abstract
The (ClCuOCuCl)-O-II-Cl-II reagent as well as the O-2/(CuOAc)-O-I syst em oxidize trimethylamine 1a into N,N-dimethyliminium 3a, characterize d by its phenolic adduct 5a. This reaction appears to be a biomimetic model for laccase or human ceruloplasmin activity towards tertiary ami nes. Amine N-oxides 2a-c react with Cu-I or Cu-II salts to give iminiu ms 3a-c, likewise trapped in good yields.